Electron transport across vesicle bilayers sensitized by pyrenes: Design and syntheses of unsymmetrically substituted bifunctional pyrenes acting as excellent sensitizers

Chemistry Letters

Volumn 32, Issue 1, 2003, Pages 68-69

  Yoshida, Asako ^a   Harada, Akitomo ^a   Mizushima, Tadashi ^a   Murata, Shigeru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRENE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; ELECTRON TRANSPORT; HYDROPHILICITY; HYDROPHOBICITY; SENSITIZATION; SYNTHESIS;

EID: 0037419615     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.68     Document Type: Article

References (15)

1. For a review, see: J. N. Robinson and D. J. Cole-Hamilton, Chem. Soc. Rev., 20, 49 (1991).
2. T. Mizushima and S. Murata, Annual Meeting on Photochemistry, Sapporo, September 2000, Abstr., p 97.
3. (a) A. A. Krasnovsky, A. N. Semenova, and V. V. Nikandrov, Photobiochem. Photobiophys., 4, 227 (1982).
4. b) A. Nakamura, R. Nishimura, K. Yoneyama, T. Ueda, and F. Toda, Nippon Kagaku Kaishi, 1988, 1208.
5. +. formation sensitized by 1-(aminomethyl)pyrene (2a) in the vesicle solution was determined to be 0.10 using a photon counter under irradiation with light of 365 nm of a 500-W extra-high pressure mercury lamp.
6. (a) M. Aikawa, N. J. Turro, and K. Ishiguro, Chem. Phys. Lett., 222, 197 (1994).
7. b) L. Li and L. K. Patterson, Photochem. Photobiol., 62, 51 (1995).
8. (a) D. C. Dong and M. A. Winnik, Photochem. Photobiol., 35, 17 (1982).
9. b) D. C. Dong and M. A. Winnik, Can. J. Chem., 62, 2560 (1984).
10. For example, the value of Py, which is defined as the ratio of the intensity of the 0-0 band of pyrene fluorescence observed in the range of 370-400 nm to that of the 0-2 band, is evaluated to be 2.19 for 2a in the vesicle solution prepared in the manner described in the text. The values of Py of 2a are 2.87, 2.29, 1.97, and 1.86 in water, acetonitrile, methanol, and chloroform, respectively.
11. (a) E. Steckhan and T. Kuwana, Ber. Bunsen-Ges., 78, 253 (1974).
12. b) W. E. Ford, J. W. Otvos, and M. Calvin, Nature, 274, 507 (1978).
13. 3) δ 0.87 (3H, t, J = 7.0 Hz), 1.27-1.31 (6H, m), 1.37 (2H, quintet, J = 7.4 Hz), 1.48 (2H, quintet, J = 7.4 Hz), 1.84 (2H, quintet, J = 7.7 Hz), 2.92 (2H, t, J = 8.1 Hz), 3.32 (2H, t, J = 7.8Hz), 3.70 (2H, t, J = 8.0 Hz), 7.86 (1H, d, J = 7.8 Hz), 7.89 (1H, d, J = 7.8 Hz), 8.05 (1H, d, J = 9.2 Hz), 8.08-8.11 (3H, m), 8.20 (1H, d, J = 9.4 Hz), 8.24 (1H, d, J = 9.4 Hz).
14. 3) δ 0.88 (3H, t, J = 6.9 Hz), 0.99-1.34 (14H, m), 1.36-1.39 (2H, m), 1.48 (2H, quintet, J = 7.6Hz), 1.85 (2H, quintet, J = 7.5 Hz), 2.93 (2H, t, J = 7.9 Hz), 3.34 (2H, t, J = 7.8Hz), 3.71 (2H, t, J = 7.9 Hz), 7.87 (1H, d, J = 8.0 Hz), 7.90 (1H, d, J = 8.0 Hz), 8.06 (1H, d, J = 9.2 Hz), 8.09-8.12 (3H, m), 8.21 (1H, d, J = 8.9 Hz), 8.25 (1H, d, J = 9.2 Hz).
15. - (1.0M).